Enantioselective synthesis of (−)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction. Issue 1 (29th October 2015)

• Record Type: Journal Article
• Authors: Franchino, Allegra; Jakubec, Pavol; Dixon, Darren J.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 1(2016)
• Page Start: 93
• Page End: 96
• Publication Date: 2015-10-29
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02141c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A concise synthesis of (−)-chloramphenicol, based on the catalytic asymmetric aldol reaction between 4-nitrobenzaldehyde and benzhydryl isocyanoacetate, is reported. Abstract : The highly enantio- and diastereoselective aldol reaction of isocyanoacetates catalysed by Ag2 O and cinchona-derived amino phosphines applied to the synthesis of (−)- and (+)-chloramphenicol is described. The concise synthesis showcases the utility of this catalytic asymmetric methodology for the preparation of bioactive compounds possessing α-amino-β-hydroxy motifs.